{{Chembox | verifiedrevid = 424770522 | ImageFile = Dithiooxamide.svg | ImageSize = 160px | ImageAlt = Structural formula of dithiooxamide | ImageFile1 = Dithiooxamide 3D ball.png | ImageSize1 = 170px | ImageAlt1 = Ball-and-stick model of the dithiooxamide molecule | PIN = Ethanedithioamide | OtherNames = dithiooxamide, rubeanic acid |Section1={{Chembox Identifiers | InChI = 1/C2H4N2S2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) | InChIKey = OAEGRYMCJYIXQT-UHFFFAOYAT | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C2H4N2S2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OAEGRYMCJYIXQT-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo = 79-40-3 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = HE28T8Z08D | PubChem = 2777982 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2058248 | SMILES = S=C(N)C(=S)N }} |Section2={{Chembox Properties | C=2 | H=4 | N=2 | S=2 | Appearance = | Density = 1.523 g/cm<sup>3</sup> | MeltingPtC = 170 | MeltingPt_notes = decomp | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | ExternalSDS = [http://msds.chem.ox.ac.uk/DI/dithiooxamide.html External MSDS] | GHSPictograms = {{GHS07}} | GHSSignalWord = warning | HPhrases = {{HPhrases|H302|H315|H319|H335}} | PPhrases = {{PPhrases|P261|P264| P270| P271| P280| P301+P312| P302+P352 |P304+P340| P305+P351+P338| P312| P321| P330| P332+P313| P337+P313| P362| P403+P233| P405|P501}} | GHS_ref = <ref>GHS: [https://pubchem.ncbi.nlm.nih.gov/compound/2777982 PubChem]</ref> | FlashPt = | AutoignitionPt = }} }}
'''Dithiooxamide''', also known as '''rubeanic acid''', is an organic compound. It is the sulfur analog of oxamide. It acts as a chelating agent, e.g. in the detection or determination of copper.<ref>{{cite web |url=http://stainsfile.info/StainsFile/stain/pigment/rubeanic-howell.htm |title=Stainsfile - Howell's rubeanic acid for copper |website=stainsfile.info |url-status=dead |archive-url=https://web.archive.org/web/20060213210752/http://stainsfile.info/StainsFile/stain/pigment/rubeanic-howell.htm |archive-date=2006-02-13}} </ref><ref>{{Cite web|url=http://www.ojp.usdoj.gov/nij/training/firearms-training/module12/fir_m12_t05_03_f.htm|title=Strengthen science. Advance justice}}</ref> It has also been used as a building block in the synthesis of cyclen.<ref>{{OrgSynth | title = 1,4,7,10-Tetraazacyclododecane | author = David P. Reed and Gary R. Weisman | collvol = 10 | collvolpages = 667 | year = 2004 | prep = v78p0073}}</ref>
==Materials chemistry== Rubeanic acid has received much attention as a precursor to photonic or electroactive materials. It is a precursor to inorganic C-S-N rings.<ref>{{cite journal |doi=10.1039/b103303b |title=Synthesis, crystal structures, electronic structure and magnetic behaviour of the trithiatriazapentalenyl radical, C2S3N3 |date=2001 |last1=McManus |first1=Gordon D. |last2=Rawson |first2=Jeremy M. |last3=Feeder |first3=Neil |last4=Van Duijn |first4=Joost |last5=McInnes |first5=Eric J. L. |last6=Novoa |first6=Juan J. |last7=Burriel |first7=Ramon |last8=Palacio |first8=Fernando |last9=Oliete |first9=Patricia |journal=Journal of Materials Chemistry |volume=11 |issue=8 |pages=1992–2003 }}</ref> It condenses with acid chlorides to thiazoles.<ref>{{cite journal |doi=10.1021/jacs.9b08959 |title=Photostable Voltage-Sensitive Dyes Based on Simple, Solvatofluorochromic, Asymmetric Thiazolothiazoles |date=2019 |last1=Sayresmith |first1=Nickolas A. |last2=Saminathan |first2=Anand |last3=Sailer |first3=Joshua K. |last4=Patberg |first4=Shannon M. |last5=Sandor |first5=Kristin |last6=Krishnan |first6=Yamuna |last7=Walter |first7=Michael G. |journal=Journal of the American Chemical Society |volume=141 |issue=47 |pages=18780–18790 |pmid=31660737 }}</ref> It forms coordination polymers.<ref>{{cite journal |doi=10.1021/ja806799t |title=Construction of Highly Oriented Crystalline Surface Coordination Polymers Composed of Copper Dithiooxamide Complexes |date=2008 |last1=Kanaizuka |first1=Katsuhiko |last2=Haruki |first2=Rie |last3=Sakata |first3=Osami |last4=Yoshimoto |first4=Mamoru |last5=Akita |first5=Yasuyuki |last6=Kitagawa |first6=Hiroshi |journal=Journal of the American Chemical Society |volume=130 |issue=47 |pages=15778–15779 |pmid=18983147 }}</ref>
==References== <references/> {{organic-compound-stub}} Category:Thioamides